Wow, great read. It sounds like you did your fair share of relocating. I am glad that thing didn't eat your legs! We used to use a toro rear tine, and that thing would just about pull me everytime. It would grab things like roots and off we went haha.
I've used three different Gravely models, and they were all hard to handle. BCS is they way to go from my experience, they're just so expensive. Have you ever heard of Colin Seis? He's an Australian farmer that is revolutionizing no-till using mob grazing with sheep. That's the direction I want to go in.
I have not heard of Colin Seis. That sounds pretty sweet though.
I first learned about him from this Joel Salatin video: